Yes, a single Xbox can support two headsets, but the method depends on the headset type and desired connection.
Single headset: Connect directly to the controller's 3.5mm jack.
Two headsets: Use a splitter cable that plugs into the controller's 3.5mm jack and provides two separate outputs. Both users can hear game audio and use their microphones.
Single headset: Most connect directly to the console via Bluetooth or a dedicated wireless adapter.
Two headsets: Some wireless headsets (like the Xbox Wireless Headset) support simultaneous pairing with the console for two users. However, this feature isn't universal—check compatibility before purchasing.
In summary, dual-headset setups are possible on Xbox, but the specific approach varies. Check compatibility and limitations before buying.